Creative Date Night Ideas Around Boston

Our dynamic city of Boston offers a wide variety of both simple and creative options for the perfect date night out. Whether you’re planning a first date or celebrating an anniversary, there are countless ways to spark some romance around our charming city, and The Overlook at St. Gabriel’s is a great jumping off point.

Have a Picnic

Bundle up and order your favorite foods to-go from one of Brighton’s many local restaurants, and head over to Fidelis Way Park for an intimate picnic. The best part?This option can be found less than a mile from The Overlook at St. Gabriel’s. If you don’t feel like venturing out, you can also enjoy an at-home picnic at The Overlook’s Promenade Lounge, complete with a fireplace to keep you warm.

Take a Virtual Cooking Class

Looking to try something new? Bring out your inner chef and impress your date during a virtual cooking class. Whisk, stir and mix your way into their heart with a gourmet class from local restaurant, Eataly, or head to Airbnb Experiences or Cozymeal. You can quickly grab all the ingredients you need from Whole Foods Market, just a 4-minute drive away from The Overlook.

Stroll Through the Boston Public Garden

Known as the first public botanical garden in America, the historic Boston Public Garden features Victorian-style statues, an abundance of unique trees and plants, colorful flower displays, a 4-acre pond with swan boats and lengthy walking paths, making for the perfect scenic afternoon stroll with your sweetheart.

Enjoy a Virtual Movie Screening

Pop the popcorn, throw on your comfiest sweats and treat your companion to a cozy movie night with the iconic Coolidge Corner Theatre! While they’re temporarily closed to in-person showings, they’re still offering virtual screenings of cult classics for a small fee. It’s a promising way to entertain your date AND support a local business!

Pick Up a Meal Kit

Don’t just order your favorite food for takeout, cook it! Many places in Boston’s eclectic restaurant scene offer DIY meal kits for an at-home cooking experience. Some popular spots near The Overlook include, Brato Brewhouse & Kitchen, Buenas Maxi Kioska and Lincoln Tavern & Restaurant.

Surprise Them with a Custom Bouquet

Sometimes, it’s the small gestures that can make the biggest difference! Whether you’re staying in or heading out, start your date night properly by surprising them with a fresh bouquet of blooms from Land’s Sake, home to over 100 varieties of flowers that you can pick yourself. You’re sure to land a second date when you live in Brighton at The Overlook at St. Gabriel’s. Schedule a tour of our astonishingly unique community today


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